New vat dyestuffs



latentecl Sept. 15, 1931 sear ICE

HANS HEYNA, OF FRANKFORT ON THE-MAIN-EGGHQ/l, GERMANY, ASSIGNOR TO GEN- ERAL ANILINE WORKS, 115G, OF NEW .Y ORK, N. 55., A CGR-PORATIO'N OF DELAWARE NEVT VAT DYESTUFFS No Drawing. Application nee June 19, 1830, Serial No. 462,425, and in Germany July 8, 1929.

The present invention relates to the new dyestuffs of the following generalformula:

CH3 CH3 oo 00 X C:/

s s X methyl or halogen With a reactive 2-derivative of a 4:-methyl-5-7dihalogen-2.3-diketodihydroxythionaphthenequinone.

As is known to the art the condensation is preferably carried out at an elevated tem perature as for instance ata temperature between about TO HO C. and advantageously in the presence of a solvent as for instance glacial acetic acid, chlorobenzene and so on.

The new dyestulis are distinguished by good fastness to light, to Washing and to chlorine, and above all by their vivid brilliant red tints.

The following examples illustrate the in vent-ion. but they are not intended to limit it thereto the parts being by Weight:

1. 36.5 parts of t-methyl-5.7dichl0ro-2.- diketo dihydrothionaphthenequinone 2 (p-dimethylamino) -anil are heated together with 20 parts of 4-methyl-6-chloro-8-hydronythionaphthene in 500 parts of glacial acetic acid at a temperature of C. for 10 hours. After cooling the dyestuff of the following formula:

to chlorine. I

2. 36.5 parts of l-methyl-5.7-d1chloro-23- diketodihydrothionaphthenequinone 2 -(p- I dimethylamino) -anil are heatedtogether With 18 parts of 4.6 vdimethyl -'3 hydroxythionaphthene in 500 parts of glacial acetic acid at a temperature of 70 C. for 10 hours. After cpoling the dyestufi' of the following formn a:

is filtered by suction and Washed until neutral. It dyes cotton very vivid bluish-pink tints of excellent fastness to, Washing and to chlorine.

3. 33 parts of a-methyl-6-chloro-23-diketodihydrothionaphthenequinone- 2 (para-dimethylamino) -anil are heated With 33 parts? 4c. 31 parts of 45.6-dimethyl-2;Sediketodihydrothioriaphthenequinone-2- (para-dimethyL I amino)-anil are heated at 70 C. with 83 parts of 4-methyl-5 J-dibromo-3-hydroxythionaphthene in 500 parts of glacial aceticacid until the formation of the dyestufi is finished. After cooling the dyestufi is filtered With suction and washed until neutral. It dyes cotton a pink tint similar to that obtained according to Example 2. It has the formula:

oo oo o=o 's \s CH3 CO G0 a! S/ \S 6. 38 parts of 4-methyl-6-bromo-2.3 diketodihydrothionaphthenequinone 2 (paradimethylamino) -anil are heated with 28 parts or 4 methyl-5-chloro-7-bromo 3 hydroxythionaphthene in 500 parts of glacial acetic acid until the formation of the dyestuff is finished. After cooling, the dyestufl is filtered with suction and washed until neu tral. It dyes cotton pink tints having properties similar to those obtained according to Example 5. The dyestuff has the formula:

I claim: 1. As new products the compounds of the following general formula:

wherein X represents halogen and Y stands for methyl or halogen possessing good fastness properties and vivid brilliant red tints.

2. As new products the compounds of the following general formula:

ons on3 X oo E c/oo s s Y wherein X stands for chlorine or bromine and Y for methyl chlorine or bromine posessing good fastness properties and vivid brilliant red tints.

3. As a new product the compound of the following formula:

dyeing cotton a beautiful vividbluish-pink tint of good fastness to light, washing, and to chlorine.

4. As a new product, the compound of the following formula:

on o 0 on;

a g t \a I) 8/ \8 Br Br dyeing cotton beautiful vivid bluish pink tints of good fastness to washing and to chlorine.

5. As a new product, the compound of the following formula:

([111 ]O 0 CH c1 S/ CH:

dyeing cotton very vivid bluish-pink tints of excellent fastness to washing and to chlorlne.

In testimony whereof, I aflix my signature.

HANS HEYNA. 

